Crystal structure of (2S)-3-methyl-2-[(naphthalen-1-ylsulfon-yl)amino]-butanoic acid.

The title compound, C15H17NO4S, was synthesized from l-valine and naphthalene-1-sulfonyl chloride. The hydrogen-bonded carb-oxy-lic acid groups form a catemer C(4) motif extending along [100]. The catemer structure is reinforced by a rather long N-H⋯O hydrogen bond, between the sulfamide N-H group and a carb-oxy-lic acid O atom [H⋯O = 2.52 (2) Å], and a C-H⋯O hydrogen bond.

Related literature

For related structures, see: Aguilar-Castro et al. (2004 ▸); Arshad et al. (2012 ▸); Mubashar-ur-Rehman et al. (2013 ▸).

Experimental

Crystal data

C15H17NO4S

M = 307.35

Orthorhombic,

a = 5.5006 (3) Å

b = 13.7638 (8) Å

c = 20.2148 (14) Å

V = 1530.45 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 296 K

0.38 × 0.22 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▸) T min = 0.920, T max = 0.956

7706 measured reflections

3290 independent reflections

2692 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.095

S = 1.02

3290 reflections

198 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.24 e Å−3

Absolute structure: Flack x determined using 919 quotients [(I +)-(I -)]/[(I +)+(I -)] (Parsons et al., 2013 ▸)

Absolute structure parameter: −0.05 (5)

Data collection: APEX2 (Bruker, 2007 ▸); cell refinement: SAINT (Bruker, 2007 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸) and PLATON (Spek, 2009 ▸); software used to prepare material for publication: WinGX (Farrugia, 2012 ▸) and PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015007057/gk2628sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015007057/gk2628Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015007057/gk2628Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015007057/gk2628fig1.tif

View of the asymmetric unit of title compound with the atom numbering scheme. The displacement ellipsoids are drawn at the 50% probability level. H-atoms are shown as small circles of arbitrary radii.

Click here for additional data file.

PLATON . DOI: 10.1107/S2056989015007057/gk2628fig2.tif

The partial packing (PLATON; Spek, 2009) which shows that mol­ecules form one dimensional polymeric network with different hydrogen-bond ring motifs. n class="Disease">H atoms not involved in hydrogen bonding are omitted for clarity.

CCDC reference: 1058549

Additional supporting information: crystallographic information; 3D view; checkCIF report

C15H17NO4S	Dx = 1.334 Mg m−3
Mr = 307.35	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 2692 reflections
a = 5.5006 (3) Å	θ = 3.1–27.0°
b = 13.7638 (8) Å	µ = 0.23 mm−1
c = 20.2148 (14) Å	T = 296 K
V = 1530.45 (16) Å3	Needle, colorless
Z = 4	0.38 × 0.22 × 0.20 mm
F(000) = 648

Bruker Kappa APEXII CCD diffractometer	3290 independent reflections
Radiation source: fine-focus sealed tube	2692 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
Detector resolution: 7.80 pixels mm-1	θmax = 27.0°, θmin = 3.1°
ω scans	h = −6→7
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −10→17
Tmin = 0.920, Tmax = 0.956	l = −21→25
7706 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.095	w = 1/[σ2(Fo2) + (0.0423P)2 + 0.0587P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
3290 reflections	Δρmax = 0.22 e Å−3
198 parameters	Δρmin = −0.24 e Å−3
0 restraints	Absolute structure: Flack x determined using 919 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.05 (5)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
S1	0.22778 (13)	0.44851 (5)	0.11598 (4)	0.0360 (2)
O1	0.8107 (4)	0.63127 (18)	−0.00511 (13)	0.0473 (6)
H1	0.836 (7)	0.692 (3)	−0.008 (2)	0.071*
O2	0.4319 (5)	0.67953 (17)	0.01812 (14)	0.0549 (7)
O3	−0.0306 (4)	0.43808 (16)	0.11995 (12)	0.0463 (6)
O4	0.3786 (4)	0.36514 (16)	0.12075 (12)	0.0509 (6)
N1	0.2790 (4)	0.49709 (18)	0.04429 (12)	0.0328 (6)
H1A	0.180 (5)	0.539 (2)	0.0325 (16)	0.039*
C1	0.5806 (6)	0.6161 (2)	0.01096 (15)	0.0349 (7)
C2	0.5237 (5)	0.5091 (2)	0.01805 (15)	0.0329 (7)
H2	0.6386	0.4809	0.0497	0.039*
C3	0.5555 (6)	0.4565 (3)	−0.04864 (19)	0.0510 (9)
H3	0.7206	0.4699	−0.0644	0.061*
C4	0.3806 (8)	0.4953 (4)	−0.0997 (2)	0.0839 (15)
H4A	0.4062	0.4623	−0.1409	0.126*
H4B	0.4077	0.5637	−0.1056	0.126*
H4C	0.2168	0.4847	−0.0850	0.126*
C5	0.5323 (12)	0.3476 (3)	−0.0401 (3)	0.105 (2)
H5A	0.6424	0.3261	−0.0063	0.158*
H5B	0.5711	0.3159	−0.0811	0.158*
H5C	0.3687	0.3318	−0.0276	0.158*
C6	0.3219 (5)	0.5300 (3)	0.17904 (16)	0.0410 (8)
C7	0.5143 (6)	0.5024 (3)	0.21720 (19)	0.0572 (10)
H7	0.5961	0.4449	0.2077	0.069*
C8	0.5895 (8)	0.5597 (4)	0.2704 (2)	0.0786 (15)
H8	0.7216	0.5402	0.2959	0.094*
C9	0.4737 (8)	0.6422 (4)	0.2851 (2)	0.0762 (15)
H9	0.5258	0.6789	0.3211	0.091*
C10	0.2755 (8)	0.6745 (3)	0.24761 (19)	0.0611 (11)
C11	0.1958 (6)	0.6187 (2)	0.19223 (17)	0.0447 (8)
C12	−0.0009 (7)	0.6539 (3)	0.1546 (2)	0.0542 (10)
H12	−0.0554	0.6185	0.1183	0.065*
C13	−0.1127 (9)	0.7393 (3)	0.1708 (2)	0.0769 (14)
H13	−0.2395	0.7624	0.1447	0.092*
C14	−0.0376 (13)	0.7922 (3)	0.2262 (3)	0.0939 (19)
H14	−0.1174	0.8495	0.2375	0.113*
C15	0.1496 (11)	0.7608 (4)	0.2635 (2)	0.0829 (17)
H15	0.1967	0.7965	0.3003	0.099*

	U11	U22	U33	U12	U13	U23
S1	0.0350 (4)	0.0333 (4)	0.0397 (4)	−0.0026 (4)	0.0009 (3)	0.0062 (4)
O1	0.0410 (14)	0.0304 (12)	0.0705 (17)	−0.0076 (11)	0.0045 (11)	0.0069 (13)
O2	0.0536 (15)	0.0311 (12)	0.0799 (19)	0.0074 (13)	0.0100 (13)	0.0071 (13)
O3	0.0354 (11)	0.0510 (13)	0.0525 (14)	−0.0103 (10)	0.0034 (10)	0.0064 (13)
O4	0.0541 (13)	0.0363 (12)	0.0622 (16)	0.0081 (11)	0.0020 (13)	0.0133 (13)
N1	0.0310 (13)	0.0309 (13)	0.0364 (14)	0.0026 (12)	0.0001 (11)	0.0053 (11)
C1	0.0378 (17)	0.0315 (17)	0.0354 (17)	0.0015 (15)	−0.0021 (14)	0.0008 (14)
C2	0.0307 (16)	0.0291 (16)	0.0390 (18)	−0.0006 (13)	0.0007 (13)	0.0041 (15)
C3	0.0468 (19)	0.044 (2)	0.062 (2)	−0.0076 (18)	0.0161 (17)	−0.0155 (19)
C4	0.087 (3)	0.120 (4)	0.045 (3)	−0.014 (3)	−0.002 (2)	−0.024 (3)
C5	0.152 (5)	0.045 (3)	0.119 (5)	−0.008 (3)	0.042 (4)	−0.031 (3)
C6	0.0362 (17)	0.052 (2)	0.0351 (18)	−0.0101 (15)	0.0041 (13)	0.0047 (15)
C7	0.041 (2)	0.081 (3)	0.050 (2)	−0.005 (2)	−0.0005 (16)	0.004 (2)
C8	0.054 (2)	0.135 (5)	0.048 (3)	−0.023 (3)	−0.010 (2)	0.004 (3)
C9	0.077 (3)	0.111 (4)	0.040 (2)	−0.040 (3)	−0.001 (2)	−0.011 (3)
C10	0.076 (3)	0.064 (2)	0.044 (2)	−0.030 (3)	0.018 (2)	−0.0049 (19)
C11	0.053 (2)	0.0432 (19)	0.0378 (18)	−0.0135 (18)	0.0101 (16)	−0.0006 (16)
C12	0.068 (2)	0.047 (2)	0.047 (2)	0.005 (2)	0.0091 (19)	−0.0024 (19)
C13	0.102 (3)	0.058 (3)	0.071 (3)	0.023 (3)	0.023 (3)	0.004 (2)
C14	0.157 (6)	0.045 (3)	0.079 (4)	0.011 (3)	0.047 (4)	−0.007 (3)
C15	0.136 (5)	0.056 (3)	0.056 (3)	−0.027 (3)	0.026 (3)	−0.020 (2)

S1—O4	1.419 (2)	C5—H5C	0.9600
S1—O3	1.431 (2)	C6—C7	1.364 (4)
S1—N1	1.621 (3)	C6—C11	1.430 (5)
S1—C6	1.775 (3)	C7—C8	1.397 (6)
O1—C1	1.323 (4)	C7—H7	0.9300
O1—H1	0.85 (4)	C8—C9	1.335 (7)
O2—C1	1.205 (4)	C8—H8	0.9300
N1—C2	1.456 (4)	C9—C10	1.401 (6)
N1—H1A	0.83 (2)	C9—H9	0.9300
C1—C2	1.513 (4)	C10—C15	1.412 (6)
C2—C3	1.540 (5)	C10—C11	1.426 (5)
C2—H2	0.9800	C11—C12	1.408 (5)
C3—C4	1.508 (6)	C12—C13	1.366 (5)
C3—C5	1.514 (6)	C12—H12	0.9300
C3—H3	0.9800	C13—C14	1.400 (7)
C4—H4A	0.9600	C13—H13	0.9300
C4—H4B	0.9600	C14—C15	1.347 (7)
C4—H4C	0.9600	C14—H14	0.9300
C5—H5A	0.9600	C15—H15	0.9300
C5—H5B	0.9600
O4—S1—O3	119.71 (14)	C3—C5—H5C	109.5
O4—S1—N1	107.01 (14)	H5A—C5—H5C	109.5
O3—S1—N1	105.33 (14)	H5B—C5—H5C	109.5
O4—S1—C6	106.96 (16)	C7—C6—C11	120.6 (3)
O3—S1—C6	108.23 (15)	C7—C6—S1	117.2 (3)
N1—S1—C6	109.32 (14)	C11—C6—S1	122.2 (2)
C1—O1—H1	109 (3)	C6—C7—C8	120.5 (4)
C2—N1—S1	122.2 (2)	C6—C7—H7	119.7
C2—N1—H1A	115 (2)	C8—C7—H7	119.7
S1—N1—H1A	115 (2)	C9—C8—C7	120.7 (4)
O2—C1—O1	124.3 (3)	C9—C8—H8	119.7
O2—C1—C2	123.6 (3)	C7—C8—H8	119.7
O1—C1—C2	112.0 (3)	C8—C9—C10	121.4 (4)
N1—C2—C1	109.6 (2)	C8—C9—H9	119.3
N1—C2—C3	111.8 (2)	C10—C9—H9	119.3
C1—C2—C3	110.5 (3)	C9—C10—C15	121.7 (5)
N1—C2—H2	108.3	C9—C10—C11	119.6 (4)
C1—C2—H2	108.3	C15—C10—C11	118.7 (4)
C3—C2—H2	108.3	C12—C11—C10	118.4 (4)
C4—C3—C5	112.0 (4)	C12—C11—C6	124.5 (3)
C4—C3—C2	111.1 (3)	C10—C11—C6	117.2 (3)
C5—C3—C2	110.8 (3)	C13—C12—C11	120.8 (4)
C4—C3—H3	107.5	C13—C12—H12	119.6
C5—C3—H3	107.5	C11—C12—H12	119.6
C2—C3—H3	107.5	C12—C13—C14	120.4 (5)
C3—C4—H4A	109.5	C12—C13—H13	119.8
C3—C4—H4B	109.5	C14—C13—H13	119.8
H4A—C4—H4B	109.5	C15—C14—C13	120.4 (5)
C3—C4—H4C	109.5	C15—C14—H14	119.8
H4A—C4—H4C	109.5	C13—C14—H14	119.8
H4B—C4—H4C	109.5	C14—C15—C10	121.2 (5)
C3—C5—H5A	109.5	C14—C15—H15	119.4
C3—C5—H5B	109.5	C10—C15—H15	119.4
H5A—C5—H5B	109.5
O4—S1—N1—C2	−44.2 (3)	S1—C6—C7—C8	−176.0 (3)
O3—S1—N1—C2	−172.6 (2)	C6—C7—C8—C9	0.4 (6)
C6—S1—N1—C2	71.3 (3)	C7—C8—C9—C10	−0.6 (7)
S1—N1—C2—C1	−115.5 (3)	C8—C9—C10—C15	178.9 (4)
S1—N1—C2—C3	121.6 (3)	C8—C9—C10—C11	−0.4 (6)
O2—C1—C2—N1	−8.8 (4)	C9—C10—C11—C12	−178.8 (3)
O1—C1—C2—N1	172.4 (3)	C15—C10—C11—C12	1.9 (5)
O2—C1—C2—C3	114.9 (3)	C9—C10—C11—C6	1.6 (5)
O1—C1—C2—C3	−64.0 (3)	C15—C10—C11—C6	−177.8 (3)
N1—C2—C3—C4	60.0 (4)	C7—C6—C11—C12	178.6 (3)
C1—C2—C3—C4	−62.4 (4)	S1—C6—C11—C12	−4.7 (4)
N1—C2—C3—C5	−65.3 (4)	C7—C6—C11—C10	−1.8 (5)
C1—C2—C3—C5	172.3 (4)	S1—C6—C11—C10	174.9 (2)
O4—S1—C6—C7	2.0 (3)	C10—C11—C12—C13	0.0 (5)
O3—S1—C6—C7	132.3 (3)	C6—C11—C12—C13	179.6 (4)
N1—S1—C6—C7	−113.5 (3)	C11—C12—C13—C14	−1.7 (6)
O4—S1—C6—C11	−174.8 (2)	C12—C13—C14—C15	1.6 (8)
O3—S1—C6—C11	−44.5 (3)	C13—C14—C15—C10	0.4 (8)
N1—S1—C6—C11	69.7 (3)	C9—C10—C15—C14	178.6 (4)
C11—C6—C7—C8	0.9 (5)	C11—C10—C15—C14	−2.1 (7)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2i	0.85 (4)	1.86 (4)	2.701 (3)	173 (4)
N1—H1A···O1ii	0.83 (2)	2.52 (2)	3.323 (3)	166 (3)
C2—H2···O3iii	0.98	2.38	3.348 (4)	169

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
O1H1O2i	0.85(4)	1.86(4)	2.701(3)	173(4)
N1H1AO1ii	0.83(2)	2.52(2)	3.323(3)	166(3)
C2H2O3iii	0.98	2.38	3.348(4)	169

Symmetry codes: (i) ; (ii) ; (iii) .